It’s July 2016. At Los Angeles art gallery Blum and Poe – the same venue that hosted Kanye West’s Famous sculpture – the air tingles with the sweet smoke of cognac-brined hotdogs and marijuana. Reggae plays on the patio, and the sprinkling of guests seems outnumbered by the security guards hulking against the dusk.

In a small back gallery hangs a lineup of 16 framed issues of High Times – the world’s foremost weed-focused publication – pulled from the archive by artist Richard Prince. Across the room, two employees from the high-end medical marijuana growers, Nameless Genetics, pack souvenir joints of their latest product, a boutique strain of weed called John Dogg, bred in the Prince’s honor and named after his alter ego. Go big on terps – AKA terpenes, the aromatic hydrocarbons that give marijuana its flavor – and John Dogg is the result. It’s an interesting mix: Blum and Poe; counterculture stalwart High Times; nu-age grower Nameless Genetics, and Prince. And it’s a meeting of the minds concocted by self-described “creative cannabis agency” Green Street.

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Among the many ganjapreneurs looking to cash in on legal weed, Green Street has an unusually cultivated pitch. “I saw an opportunity to come into an industry and really create some great visual moments with artists and brands,” says creative director Darren Romanelli, who has collected contemporary art for around a decade. Romanelli, aka DRx, who also runs ad firm StreetVirus, is a marketing veteran, with clients from Coca-Cola to the Grateful Dead. Cross-pollinations with designers and visual artists have always been his specialty. A few years ago, during a campaign for vape brand Grenco Science (makers of the G-Pen), the path became clear.

“We noticed that there wasn’t a lot of great branding and great packaging,” he says, “and a lot of the imagery and artwork ... felt a little lowbrow.” Romanelli and three others co-founded Green Street in 2013 to provide an option for those who wanted something different. “We wanted to bring some professionalism into what felt like an otherwise unprofessional space – very much the wild west.”

Green Street keeps offices in the penthouse of the historic art deco Wilshire Tower. Up the stairs, past an open-air kitchen where the firm hosts private release events – “activations,” in their argot – is a rooftop lounge surveying mid Los Angeles. The north parapet is tipped by a flagpole, which has become, in Green Street fashion, an occasion for artist projects. During the opening of a permanent installation by Kenny Scharf – a concrete hallway painted white, rigged with blacklights, and curlicued with the artist’s signature bug-eyed blobs and galaxies – they hoisted a flag Scharf made back in 1988: a druggy, grinning compass rose.

Fast forward to late November. Up the pole is a lightly frayed American flag. Proposition 64, a California ballot initiative, has effectively legalized cannabis statewide, some 20 years after the Compassionate Care Act sanctioned limited medical use. Yet there are gathering clouds: President-elect Trump’s nascent federal administration counts Nixonite drug warrior Jeff Sessions among its white nationalists. (Most colorfully, Sessions joked that he thought the Ku Klux Klan were OK folks until he found out they smoked weed. He’s also on the record saying: “Good people don’t smoke marijuana.”) But cannabis law has always been a bit hazy. In 2010, even as Obama moved to decriminalize, the Drug Enforcement Agency momentarily stepped up raids. Green Street partner and legal counsel, Joshua Shelton, who also represents dispensaries, says he never tells his clients they’re fully in the clear. In states where weed is legal, new regulations can be confusing and untested. Meanwhile, at the federal level, marijuana remains a schedule I controlled substance – the highest classification, on par with heroin, and a notch above methamphetamine.

Despite the gray areas, Shelton compares the momentum of regulated cannabis to a snowball that, “at this point,” he says, “I’d be scared to stand in front of. These are self-made millionaires. They’re literally the American dream of a businessman.” But the problem is they’ve never done official business. Building an above-ground identity means courting more than the gas mask bong set – the new generation of legal weed companies needs branding. Passé, too, are the crass, low-budget sexy-nurse weed ads stuffing the high-numbered pages of the LA Weekly. For growers, advertising used to be dangerous. Now, it’s existential. Among those committed to what Romanelli calls “elevating” the industry, Colorado-based Cannabrand stands out for general professionalism and accessibility, while the clean-lined billboards of breeder THC Design are a far cry from shots of bikinis and buds.

Romanelli and Shelton’s first effort, arranging for Snoop Dogg to use the G-Pen vaporizer, is typical of the kind of social-media promotions favored by companies still shunned by TV and web. But endorsements from the avowed stoners of hip-hop and skate culture aren’t exactly groundbreaking. Enter “high art”. Green Street hopes established rebels like Scharf and Prince will lend weed and its derivatives a respectable aura. (They’re currently working on a Dennis Hopper Cannabis Company with the late actor’s estate.)

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Indeed, pairing art with marijuana is a natural idea – one that artists hit on long ago. “I did a large grow in my backyard in 1996 to help support me when the gallery was barely making it,” says Blum and Poe co-founder Jeff Poe. “As for the material itself: weed is transformative, experiential, performative, idea driven.” Sounds like art. And if Green Street’s pairings so far have felt a bit awkward, in the way that only shameless marketing can, it’s nonetheless a noble goal to one day admit cannabis to the club of refined, almost culinary taste.

Prince made his Hippie Drawings in the late 90s, during the country’s last acute bout of psychedelia – and a heyday for branding. “I was hooking up with the cartoon again,” says Prince. “Just started drawing my own cartoon over existing cartoons. Hippie Families. Something like that.” They were published in a small-run catalog, but never shown. Then, a couple of years ago, as if part of the conversation all along, the drawings resurfaced: “I heard from High Times,” says the artist. “They asked. I agreed.”

Gracing the covers of the High Times Special Trippy Issue are three of Prince’s Hippie Drawings, purposively naive, like an arguably stable 21st century man trying to doodle like an electroshock victim. The most widely circulated design bears a pink-skinned, clutch-armed rag doll with beer tabs for eyes and a wonderful long cigarette. For Prince and High Times both, their collaboration marks a wider, cyclical regurgitation, wherein counterculture sheds the “counter” part. But wasn’t that always the dream?